1,2-Dichloroethane → (3R)-tert-butyl 3-(methoxy(methyl)carbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

HRID 1371520노트

반응식

HRID 1371520 반응식
[N:1]1([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C@@H:2]1[C:11]([OH:13])=O.Cl.[CH3:22]OCN.C(Cl)CCl.C1C=C[C:33]2[N:38]([OH:39])N=NC=2C=1.CCN(C(C)C)C(C)C>C(OCC)(=O)C.C1COCC1>[N:1]1([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C@@H:2]1[C:11]([N:38]([O:39][CH3:22])[CH3:33])=[O:13]

참가 물질

8

반응물 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 688607(3R)-2-[(tert-butoxy)carbonyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acidHCID 21959107Methoxymethanamine hydrochloride

생성물 1

HCID 86597541(3R)-tert-butyl 3-(methoxy(methyl)carbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate수율 71.5%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

Boc-D-Tic-OH (14.9 g, 53.7 mmol), methoxymethylamine hydrochloride (5.24 g, 53.7 mmol), EDC (11.3 g, 59.1 mmol); HOBT (7.98 g, 59.1 mmol), DIPEA (9.83 ml, 59.1 mmol) and THF (500 ml) are combined, and the resulting mixture is stirred for about 18 hours at r.t. under nitrogen. The mixture is stripped to dryness, and the residue is taken up in ethyl acetate. The resulting mixture is washed with 1M HCl, saturated NaHCO3 and brine, and then dried. Solvent is removed and the residue is chromatographed on normal phase using 1:1 ethylacetate/hexane to give about 12.3 g of Boc-D-Tic-NMeOMe (Weinreb amide).

후처리

  1. washThe resulting mixture is washed with 1M HCl, saturated NaHCO3 and brine
  2. customdried
  3. customSolvent is removed
  4. customthe residue is chromatographed on normal phase

출처 및 근거

ORD 기록
ord-b5ebed1fb6df4e2680ba4587046d7198
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07157463B2

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